


#9: Dean WInchester/Sam Winchester (Supernatural)

by DeansTrapQueen



Series: Merry Month of Masturbation 2016 [9]
Category: Supernatural
Genre: M/M, Masturbation, Merry Month of Masturbation Challenge, Voyeurism, Weecest, Wincest - Freeform, i don't really know what to call this, pillow fucking (?)
Language: English
Status: Completed
Published: 2016-05-13
Updated: 2016-05-13
Packaged: 2018-06-08 02:26:57
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 1,255
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6835255
Author URL: https://archiveofourown.org/users/DeansTrapQueen/pseuds/DeansTrapQueen





	#9: Dean WInchester/Sam Winchester (Supernatural)

     "Alright, Dad. Yes, I will Sir. Ok, love you. Bye Dad." Dean hangs up the phone and sighs.

     "Well?" Sam puts his hands on his hips and waits for his big brother to answer him.

     "He won't be back for another week." Sam frowns and nods.

     "I guess it's good that Dad isn't coming back yet, right? I'll get to stay at this school a little longer." Dean smiles at his little brother and ruffles the boy's long hair. _Always tryin' to see the bright side,_ Dean thinks. _That's my Sammy._

     "Wanna go to Friendly's? You can get whatever you want," Dean says to Sammy, trying to make up for their Dad's absence. Sam's face lights up, and the boy nods. "Alright, go change. I gotta take a shower." The brothers look through their duffel bags and pull out clean clothes, and when Dean finds something to wear, he goes into the bathroom to take a shower. Sam strips out of his pajamas and puts on his outfit. Dean always teases him for wearing pajamas when he's at home, but Dean does it too. Sam sits on the edge of his bed, waiting for Dean to finish in the shower. He loves Friendly's and hasn't been there in forever, so he gets more and more impatient each minute. Suddenly, the bathroom door whips open.

     "Dean, what's wrong?" Sam asks. Dean steps out of the bathroom, naked and dripping wet. "Hey, you're gonna get the carpet all wet!" Sam exclaims. Dean waves a hand at him.

     "I just realized that the shirt I picked out is dirty," he says. He bends over to look for a different shirt. Dean and Sam saw each other naked all the time, but Sam never really took the time to study his big brother's body. It's lean and muscled from hunting, and freckles pepper his lightly tanned skin. Dean doesn't completely shave his pubic hair, but he keeps it trimmed. Sam drinks in the sight of his brother's dripping wet body. Suddenly, Dean stands up again with a shirt in his hands. "I'll be out in five minutes," he promises before going back into the bathroom. Sam sighs and leans back on the bed. He unconsciously moves a hand down to his hardening dick. _Why is Dean affecting me like this all of a sudden? This is weird. Must be the teenage hormones or something._ Sam puts on his socks shoes, and the shower turns off. He hears the hairdryer turn on a minute or two later, and Dean walks out. His hair is still slightly damp, and when he lifts his arms to ruffle his hands through it, the bottom of his shirt lifts too, revealing his v-lines. All Sam wants is to trace those lines with his tongue.

     "Hurry up!" he whines, trying to act normal again. Dean laughs and pulls on his socks and boots.

     "Alright, let's go, kid." The boys leave the motel.

* * *

* * *

     At Friendly's, Sam orders chicken tenders and macaroni and cheese, and Dean orders a burger and fries. Both brothers order a vanilla milkshake, and Sam says that he plans on getting a sundae for them to share, too. The boys eat their meal, Sam telling Dean about school, Dean telling Sam about his days in school. When they were done with their food, Dean ordered them a sundae.

     "Here's your sundae," says the waitress as she sets the bowl on the table. The boys thank her, grab their spoons, and dig in.

     "Mmm," Sam moans. His eyelids flutter closed. "This is so good. Friendly's has the best ice cream." Dean nods and clears his throat. _That was weird,_ he thinks. _That moan sounded pretty sexual. Hmm, I wonder what Sammy would sound like during sex. Bet he'd make the cutest little noises. I wonder what he'd look like. He'd probably be beautiful, as usual._ Dean is shocked by his thoughts about his 15 year old brother. "You alright, Dee?" Sam asks. Dean smiles.

     "Wonderful." Dean and Sam devour their ice cream. When Sam is eating the last little bit, he pauses to say something to Dean before putting it in his mouth. Some of the ice cream melts off the spoon. It runs down his hand, all the way down to his elbow.

     "Dammit. It's ok, Dean, I got it." Dean sets the napkin he picked up on the table. Sam brings his elbow up to his mouth and sucks the ice cream off. He works his way up to his fingers. Dean watches with his mouth slightly open and his eyes hooded. Finally, Sam finishes. Dean steadies his breath and throws some money on he table. _Jesus, what is he doing to me?_ Dean thinks.

* * *

* * *

     "G'night, Sammy."

     "Goodnight, Dee." Sam rolls over onto his right side so he isn't facing Dean. He still has a hard-on, and he can't stop thinking dirty thoughts about his brother. Dean is in the same boat; he has an erection and he can't stop thinking about Sam. Eventually, though, Dean falls into a restless sleep. Sam, on the other hand, can't sleep; his prick is too hard and uncomfortable. He puts his hand between his legs and grinds down on it, whimpering each time his hips move down. He pants, but he knows he won't come from just this. "Fuck it," he mutters. He sits up and turns around. He takes the pillow and moves it down so it's under his knees. He moves onto his stomach and adjusts himself. Finally, he finds a comfortable position. _I can't believe I'm about to fuck a pillow. Well, desperate times call for desperate measures, I guess._ He takes a deep breath and moves his hips forward. He immediately takes his boxers off and throws them on the floor. He humps the pillow slowly, imagining it's Dean's ass. He speeds up and whimpers. He needs something more, but this will have to do for now. Sam bites the sheets and moans. He tries to stay quiet so he doesn't wake Dean, but he's not sure he's doing a good job.

     Dean's eyes open slowly, his weary brain not processing the noises coming from the bed next to his. At first, he thinks Sammy is hurt. Then, he realizes that Sam is moaning and sobbing. He sits up quietly and rubs his eyes. A streetlight illuminates the room a bit, and Dean can see his little brother humping something. Dean's mouth falls open, and his hand flies down to his cock. He palms it through his boxers, feeling his pre-cum wet the fabric. Sam fucks the pillow harder and faster, and Dean slips his hand into his boxers. Sam still hasn't noticed Dean, but then Dean gasps sharply, attracting Sam's attention. The boy's head whips around, and the brother's eyes meet. Sam cries out and gasps.

     "Dean!" he screams. Then, he's sobbing and fucking the pillow frantically with his face in the bed, hidden behind his arm. His body relaxes a few seconds later, and Dean groans.

     "God, Sammy!" he yells. Cum shoots inside his boxers, staining parts of the black fabric white. Sam watches Dean orgasm. Dean's full, pink lips are open, his beautiful eyes clasped shut. Dean opens his eyes once his orgasm is over and looks at his little brother. His cheeks are red and stained with tears, his bottom lip is redder than usual because he was biting it, trying o keep himself quiet. "I was right," Dean says breathlessly. "You look _gorgeous_ when you come."


End file.
